Acetanilide → HCID 24821528, compound

HRID 1028393Notes

Reaction equation

Br[C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[C:4]([CH3:11])[N:3]=1.[C:12]1([NH:18][C:19](=O)[CH3:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[CH3:20][C:19]1[N:18]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:2]2=[N:3][C:4]([CH3:11])=[CH:5][CH:6]=[C:7]2[N:8]=1

Participants

Reactant 2

HCID 904Acetanilide

HCID 247280132-Bromo-6-methyl-3-nitropyridine

Product 1

HCID 24821528HCID 24821528, compoundYield 51.1%

Procedure

The title compound was prepared with the analogous procedure described in example 3 using 2-Bromo-6-methyl-3-nitropyridine (108 mg, 0.5 mmol) and N-phenylacetamide (81 mg, 0.6 mmol) as starting materials to yield the title compound as brown viscous oil (57 mg, 51%). 1H NMR (DMSO) δ 2.42 (s, 3 H), 3.31 (s, 3 H), 7.11 (d, J=8.0 Hz, 1 H), 7.51-7.63 (m, 5 H), 7.89 (d, J=8.0 Hz, 1 H); 13C NMR δ 14.6, 23.8, 118.0, 126.1, 127.7, 128.7, 129.4, 132.1, 134.8, 148.3, 150.9, 151.1. HRMS: cal for C14H14N3 [M+H+]: 224.1188; found: 224.1184.

Workup

customThe title compound was prepared with the analogous procedure

Sources & evidence

ORD record: ord-c16a2c1065054da1b1053edc9c4d2a1f
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735586B2

Reaction notes

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